Synthesis with benzenesulfenyl chloride. On the structure of a C12H18 hydrocarbon from East Indian sandalwood oil - ScienceDirect

Tetrahedron Letters

Volume 21, Issue 49, 1980, Pages 4711-4714

Tetrahedron Letters

https://doi.org/10.1016/0040-4039(80)88100-7 Get rights and content

Abstract

The tetracyclic hydrocarbon $1$ was synthesized by means of the electrophilic addition of benzenesulfenyl chloride to an appropriately substituted methylenenorbornene $7$ . The synthetic methodology used to prepare this letter compound includes a mild enol ether hydrolysis with acidic silica gel.

References (15)

D. Heissler et al.
Tetrahedron Lett.
(1979)
E. Demole et al.
Helv. Chim. Acta
(1976)
F.G. Bordwell et al.
M. Larcheveque et al.
J. Organomet. Chem.
(1973)
T. Cuvigny et al.
Bull. Soc. Chim. Fr.
(1973)
L.I. Zakharkin et al.
Dokl. Akad. Nauk SSSR
(1957)
Chem. Abst.
(1958)

There are more references available in the full text version of this article.

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¹: Centre National de la Recherche Scientifique.

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